4-Methoxybenzylamine → HCID 118598750, compound

HRID 1050420Notes

Reaction equation

HRID 1050420 reaction equation
Br[CH2:2][C:3]1[C:4]([C:11]([O:13]C)=O)=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1>O1CCCC1.C(OCC)(=O)C.O>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[C:11](=[O:13])[N:22]([CH2:21][C:20]3[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=3)[CH2:2][C:3]=12

Participants

6

Reactant 2

HCID 754524-MethoxybenzylamineHCID 72714266HCID 72714266, compound

Product 1

HCID 118598750HCID 118598750, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of methyl 3-(bromomethyl)-4-methoxypicolinate (1.0 mmol, 1 eq) in tetrahydrofuran with 4-methoxybenzylamine (2.0 mmol, 2 eq) and stir the reaction for 16 h. After completion dilute the mixture with ethyl acetate and water and separate the layers. Wash the organic layer with 1 M hydrochloric acid and water. Concentrate the organic layer to give crude. Purify the crude by silica gel column chromatography to afford 4-methoxy-6-(4-methoxybenzyl)-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one (2).

Workup

  1. customthe reaction for 16 h
  2. customseparate the layers
  3. washWash the organic layer with 1 M hydrochloric acid and water
  4. concentrationConcentrate the organic layer
  5. customto give crude
  6. customPurify the crude by silica gel column chromatography

Sources & evidence

ORD record
ord-b6e647f8f63b4aa1a476a4f14d766074
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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